The total synthesis of various members of the ergot family will be pursued through the use of intramolecular 3 plus 2 cycloaddition reactions of nitrones and nitrile oxides. The new compounds produced during these studies will be available for screening as potential prolactin inhibitors, antitumor and cardiovascular agents. Synthetic routes to the CNS active indolic compounds, the rugulovasines, will be examined based on a strategy involving the intramolecular Mannich type reactions of substituted silyloxyfurans. This effort will also focus on the development of new routes to gamma-lactones and butenolides. Chuangxinmycin, which represents a new indole alkaloid isolated from a microorganism found growing in a soil sample in the Shatung Province of China, is efficacious in the treatment of urinary and biliary infections. Efficient strategies for the preparation of this compound and analog structures via nitro group displacement reactions will be developed.